13C NMR Analysis of an Aqueous Electrophilic Aromatic Substitution (Synthesis of β-Resorcylic Acid)

• James A. McKee ^[1] ; Emalie Rowles ^[1] ; Yumee Koo ^[1] ; James R. McKee ^[1]
  1. [1] University of the Sciences

     University of the Sciences

     City of Philadelphia, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 100, Nº 8, 2023, págs. 2981-2985
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • Electrophilic aromatic substitution reactions are common in the organic chemistry laboratory. These reactions, while ubiquitous, use corrosive reagents and halogenated or hydrophobic solvents that produce expensive and hazardous waste streams. The carboxylation of phenols (Kolbe–Schmitt reaction), although aqueous, typically involves conditions (high pressure/temperature) that are not well-suited for a large teaching laboratory. The following experiment modifies the Kolbe–Schmitt process for ambient pressures and aqueous reflux temperatures. This procedure is safe, simple, and inexpensive and uses 13C NMR as an analytical tool to confirm product synthesis and investigate changes in molecular symmetry.